Highland Homes for Sale

Welcome to Highland, a charming neighborhood nestled in the heart of Middletown, Connecticut, within the picturesque Middlesex County. This delightful community offers a perfect blend of suburban tranquility and vibrant local culture, making it an ideal place to call home.

Highland is characterized by its tree-lined streets, friendly neighbors, and a strong sense of community. Residents enjoy easy access to a variety of parks and recreational facilities, perfect for families and outdoor enthusiasts alike. The neighborhood is also conveniently located near downtown Middletown, where you can explore a diverse range of shops, restaurants, and entertainment options. From cozy cafes to eclectic boutiques, there’s something to suit every taste.

For those considering a move to Highland, you’ll find an array of charming homes for sale that cater to various lifestyles and budgets. Whether you’re looking for a quaint single-family home with a spacious yard or a modern townhouse with contemporary amenities, Highland has it all. Many properties boast beautiful architectural details and are set against the backdrop of lush greenery, providing a serene living environment.

Highland is also known for its excellent schools and community-oriented atmosphere, making it a fantastic choice for families. With a strong commitment to education and a wealth of local resources, parents can feel confident in the opportunities available for their children.

Discover the charm of Highland and explore the homes for sale in this inviting neighborhood. Your dream home awaits in this hidden gem of Middletown!

Newest Highland Homes for Sale

$699,000

4 Beds ⋅ 3 Baths ⋅ 24197740 MLS

Nestled in the sought-after Chimney Hill neighborhood, this spacious Colonial offers over 4,200 square feet of thoughtfully designed living space on a beautifully landscaped lot. The home features 4 bedrooms, 2.5 bathrooms, a bright, open floor plan, generous living and dining areas, and a spacious kitchen perfect for everyday living and entertaining. The family room provides a warm gathering space, while the primary suite offers a private retreat with ample closet space and an en-suite bath. Additional highlights include a two-car attached garage, a large backyard ideal for outdoor entertaining, and a prime location just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, and major commuter routes. This is a rare opportunity to own a beautiful home in one of Middletown's most desirable neighborhoods.

20 Chimney Hill Rd, Middletown

$289,609

4 Beds ⋅ 2 Baths ⋅ 24177666 MLS

Welcome to this spacious move in ready four bedroom, two bath home located in the desirable Highland section of Middletown. This well maintained property features an updated kitchen with granite countertops and stainless steel appliances, offering both style and functionality. The first floor includes laminate flooring throughout the main living areas, while the bedrooms feature carpeting for added comfort. A slider in the living room provides access to the backyard and brings in plenty of natural light. With generous room sizes and a convenient location close to shopping, dining, parks, and highways, this home offers a great combination of comfort and convenience.

33 Inverness Ln, Middletown

$289,609

4 Beds ⋅ 2 Baths ⋅ 24158805 MLS

Welcome to this inviting contemporary home in Middletown offering the perfect blend of comfort, style, and convenience. This well maintained 4 bedroom, 2 bath residence features 1,328 square feet of thoughtfully designed living space ideal for today's lifestyle. Step inside to discover an updated kitchen with modern finishes, providing a functional and attractive space for everyday living and entertaining. Both bathrooms have been tastefully updated, adding a fresh, move in ready feel throughout the home. The flexible floor plan offers four bedrooms, giving plenty of room for family, guests, or a home office. One of the home's most convenient features is the second floor laundry, making daily chores easier and more efficient. With its contemporary style, smart layout, and desirable updates, this home offers a fantastic opportunity to enjoy comfortable living in a convenient location close to shopping, dining, parks, and major commuting routes. Don't miss your chance to make this beautiful Middletown home your own.

34 Inverness Ln, Middletown

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.